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$1,299,999
4 Beds 4 Baths 1031174 MLS
A private gated community surrounded by nature. This exceptional retreat offers the perfect blend of privacy, luxury, and tranquility. Enter to a spacious great room featuring a stunning stone fireplace, creating a warm and inviting gathering space. The chef’s kitchen is thoughtfully designed for both everyday living and entertaining and flows seamlessly into a beautiful sunroom overlooking the pond. Decking surrounds the home, providing the perfect setting to enjoy the peaceful outdoors. The main level includes an additional bedroom and a full bathroom. Upstairs, the private suite features an en suite bathroom, with an outside balcony offering a relaxing retreat. The finished lower level boasts two additional bedrooms, a laundry room, a spacious entertaining room, providing ample space for guests. Outside, you’ll find a luxurious stone patio complete with a spa, Jacuzzi, and a high-end outdoor kitchen, all overlooking a picturesque pond. A separate guest house offers even more flexibility, featuring a welcoming front deck, its own laundry room, and an attached two-car garage, making it perfect for visitors, or a private home office. There is an additional 3 Car detached garage and generator. This remarkable property combines charm with modern amenities in one of the area’s most peaceful and private settings. Close to trendy restaurants, quaint towns, farmers markets, fishing, hiking, casino, Holiday Mountain Ski area and Bethel Woods Center for the arts and the Callicoon movie theatre.

140 Kenoza Trail, Callicoon

$789,000
3 Beds 2 Baths 1021417 MLS
Are you tired of every house in this area looking the same-old, same-old dark color? Well, this brand-new build is a breath of fresh air! Gorgeous 3 BR/2bath custom contemporary sits on 5.25 acres in Callicoon, white in color with black trim. It really pops, and looks so different than those cookie-cutters, yet thoroughly modern! Constructed by one of the premiere builders in our area, JIT Construction, you can count on quality workmanship and an eye for detail! From the moment you pull in to the driveway, you'll see the 2-car garage attached to the home via a breezeway, which makes it easy in bad weather. Step into the house via the mudroom/laundry or the front entrance and you'll be greeted with an open floor plan: a soaring cathedral ceiling in DR/LR area. The living room has floor to ceiling glass, washing the home with natural light. A gorgeous LP gas stone fireplace takes center stage here, adding heat and creating ambience. The kitchen is a dream! Crisp white quartz counters that gleam with light accented by a gorgeous pendant light fixture... Lots of counter and cabinet space here, enough to make a chef drool! You can dine at at the island, though there's plenty of room for a table & chairs too, just beyond. Primary BR off to the right; spacious walk-in closet and a sliding door that opens to the deck. There are two other BRs and a full bath off to the left. Walk outside via the sliders in living room to find a huge deck which runs the length of the home. You'll be soothed by the peace and quiet of nature and birdsong. The home is painted in pleasing neutrals for color, but it's far from boring, as evidenced by the decorative tiles in bathrooms and the gorgeous quartz counters. Chic ceiling fans and central AC. The home is located just a couple minute's drive to Callicoon, where you'll find Delaware River access and fun, all kinds of shops and eateries, a movie theater, bowling alley, Sunday Farmers Market, supermarket, hospital, banks, and Visitors Center in the Train Station. 15 minutes south to Narrowsburg. 20 minutes to Bethel Woods Center for the Arts for concerts and cultural events.

204 Country Road, Callicoon

$315,000
3 Beds 2 Baths 1024336 MLS
We are proud to present this wonderful home in the highly sought-after Beechwoods area, renowned for its breathtaking countryside views and peaceful rural setting. This well-maintained residence features three bedrooms and one-and-a-half bathrooms, including a primary bedroom with its own private half-bath ensuite. The home also offers an attached two-car garage and a spacious basement, providing ample storage and flexibility for a variety of uses. Step outside onto the rear deck and enjoy the stunning Beechwoods views while taking in the beauty of the surrounding landscape. The property is enhanced by mature apple trees, established grapevines, and a large backyard—perfect for entertaining, gardening, or simply enjoying the outdoors. Conveniently located just minutes from the vibrant hamlets of Callicoon, Jeffersonville, Narrowsburg, Roscoe, and Livingston Manor, you’ll enjoy easy access to boutique shopping, dining, golf courses, outdoor recreation, and year-round entertainment. Whether you’re seeking a full-time residence, weekend retreat, or investment opportunity, this Beechwoods property offers the perfect blend of country charm, privacy, and convenience.

22 Kratz Road, Callicoon

$349,000
3 Beds 3 Baths 1010833 MLS
Welcome to this immaculate Beechwood Estates II condominium townhouse in Callicoon's Beechwoods hills. Pride of ownership is visible throughout. A 3 bedroom, living/dining room, eat-in kitchen, 2 full baths, and a covered porch with an open deck offer lots of space for the weekend warriors or full time residents. The attached garage and the fully finished basement with a half bath complete the picture. There is an LP operated full house generator; an alarm system; an alarm for the hot water heater, and a built-in dehumidifier in the finished basement. Enjoy golf at the Villa Roma Resort's 18 hole golf course and shop and dine at the wonderful shops and eateries you will find in Callicoon, Jeffersonville and Livingston Manor. This is a 4-season home in New York's Catskills which allows many city dwellers to cope with another busy city week. Come and take a look!

7 Villa Vista Drive Unit #702, Callicoon

$995,000
3 Beds 3 Baths 1006876 MLS
Modern luxury and serenity await you, perched high above the Hamlet of Callicoon and within 5 minutes to the center of town. Whether you are seeking a peaceful full-time residence or an elegant weekend escape, this custom-designed modern country retreat perfectly blends refined architecture with expansive indoor-outdoor living. The residence, set on 8.02 acres, features 3 bedrooms and 2.5 baths, highlighted by soaring cathedral ceilings and a seamless open floor plan. The dining area is anchored by a stunning wall of windows, offering panoramic mountain and valley views of the surrounding natural landscape. Practical amenities include a two-car detached garage with ample storage and a convenient covered walkway. The outdoor living space is designed for entertaining, featuring a bluestone patio surrounding an inground fiberglass saltwater pool and an outdoor dining lanai - all located just minutes from downtown Callicoon. The property is ideally situated near local farmers' markets, breweries, outstanding restaurants, and hiking trails. With easy access to kayaking and the vibrant Main Street of Callicoon, this home offers the perfect balance of secluded privacy and community charm. Located 2 hours from NYC.

118 Froehlich Drive, Callicoon

$355,000
3 Beds 2 Baths 1005698 MLS
Peaceful Country Retreat on Over 5 Acres Welcome to 12 Mesmer Road — a charming country home set on more than 5 scenic acres, offering privacy, tranquility, and plenty of space to enjoy the outdoors. Whether you’re searching for a full-time residence, weekend escape, or investment opportunity, this property delivers the perfect blend of comfort and countryside charm. The home features three bedrooms and two full bathrooms, along with a spacious eat-in kitchen and separate dining area ideal for family gatherings and entertaining. The oversized living room is filled with natural light thanks to a skylight and large sliding glass doors that open to the backyard patio — perfect for outdoor dining and relaxing summer evenings. Step outside to take in beautiful country views, mature trees, classic stone walls, and peaceful creeks that run throughout the property. On warm days, enjoy your own private heated in-ground pool, creating the ultimate setting for summer fun, barbecues, and quiet relaxation. Conveniently located just minutes from Callicoon, Narrowsburg, Jeffersonville, and Bethel Woods Center for the Arts, this property offers the serenity of country living while remaining close to local shops, dining, and entertainment. If you’re looking for space, privacy, and a true escape to the countryside, 12 Mesmer Road is a must-see. Schedule your private showing today!

12 Mesmer, Callicoon

$685,000
3 Beds 3 Baths 1003008 MLS
Set on 10 breathtaking acres with sweeping panoramic views, this exceptional property offers the perfect blend of comfort, privacy, and Catskills charm. The beautifully maintained home features 3 bedrooms and 3 bathrooms, thoughtfully designed living spaces, and expansive decks that showcase the stunning natural surroundings from nearly every angle. At the heart of the home is a spacious thought out kitchen complete with skylights, abundant storage, and generous counter space—an inviting space any home chef will appreciate. Sun-filled living areas feature oversized windows that frame the landscape and create a seamless connection to the outdoors. The finished lower level is designed for entertaining, featuring a full wet bar, full-size pool table, and direct access to an inviting patio and outdoor firepit area—perfect for relaxing evenings under the stars while taking in the peaceful scenery. Additional highlights include a fantastic detached two-car garage and beautifully usable acreage ideal for recreation, gardening, or simply enjoying the tranquility of nature. Conveniently located just minutes from the charming hamlet of Callicoon, and a short drive to Narrowsburg, Livingston Manor, Jeffersonville, and Roscoe, this property offers easy access to some of the region’s best shopping, dining, farmers markets, and outdoor recreation.

340 Hospital Road, Callicoon

$599,000
4 Beds 2 Baths 999372 MLS
A rare opportunity in the heart of the Catskills — this stunning 5-acre property offers a true million-dollar view, unmatched privacy, and direct access to a championship 18-hole golf course. Whether you’re dreaming of a peaceful country home, a high-earning VRBO retreat, or a charming bed-and-breakfast, this property delivers location, scenery, and potential that simply can’t be replicated. The home exudes warmth and charm. The house was gutted 11 years ago and walls were moved. so you are not buying that old house in the country, but an up to date version of it. Septic was replaced in 2025. Inside you will find a living room with a gas fireplace, an up to date kitchen with dining area and a main bedroom suite you always dreamed about. You are surrounded by Callicoon's magnificent Beechwoods. The views are spectacular. No light pollution here! Life in the country does not get any better.

519 County Route 164, Callicoon

$1,048,000
4 Beds 4 Baths 993379 MLS
Step into serene sophistication with this immaculate custom contemporary Gambrel-style country home, a true architectural showpiece blending rustic charm with modern design. The expansive open-concept living space stuns with soaring 30-foot Hemlock wood ceilings, dramatic exposed beams, and a floor-to-ceiling stone fireplace. Gleaming hardwood floors and panoramic windows flood the home with natural light, perfectly framing sweeping views of Pennsylvania and New York’s rolling countryside. Awarded Sullivan County’s 2007 Home of the Year, this 3,750 sq ft residence sits gracefully on 7.32 stone-walled private acres. The thoughtfully designed floor plan features four bedrooms and 3.5 baths, including two luxurious primary ensuites. Custom touches are everywhere: radiant heat with central A/C, a chef’s kitchen with bluestone island counters, Wolf six-burner stove, SubZero refrigerator, and Miele appliances, plus wine fridges to complete the picture. Remote Nest controls, a steam room, hot tub, and outdoor shower add everyday luxury. The lifestyle continues outdoors with terraces, open sky, half basketball/pickleball court, garden and your own private retreat. A two-story 2,000 sq ft barn-door garage provides space for cars, recreational gear, or even creative projects. There’s also a 2nd floor space to expand your imagination! Whether it’s entertaining around the fire, soaking in the hot tub, or simply enjoying quiet mornings with sunlight pouring in, this home is built for comfort and unforgettable moments. All just two hours from NYC, minutes to Callicoon and the Delaware River with its fine dining, shops, and cultural life. This Catskills treasure offers the best of both worlds—modern elegance set against timeless country beauty.

63 Sky View Drive, Callicoon

$444,000
2 Beds 2 Baths 983165 MLS
Price reduction and offer of $20k credit plus new furnace! This 26.43 acre parcel of land features a home with 2 bedrooms, 2 full baths, and a spacious loft area that serves as the 3rd bedroom. The sunny, bright great room has a cathedral ceiling. There is a full basement and a one car garage underneath. You will also find a shed and a lovely pond where only the ducks are missing! House and deck will need some TLC, and the seller is offering a $20,000 credit at closing. Seller will also replace the furnace before closing. Come and take a look and present all offers! This could be your ideal get-away from city stress if you apply some elbow grease. This is a delightful rural location for kids to ride bikes or for you to jog or walk. Pack a picnic and hike down to the creek to enjoy a dip in the water and a luncheon al fresco. There is a second clearing along W Simmon, together with substantial road frontage to subdivide or build another home. It is 10 minutes to downtown Callicoon with its eateries, shopping, entertainment, Delaware River activities and Sunday Farmers Market. Or 10 minutes to Roscoe to fly fish in your favorite streams!

10 W Simmon, Callicoon

$399,000
5 Beds 2 Baths 982483 MLS
Three story Victorian 5-BR home located on the end of a quiet cul-de-sac overlooking the bustling village of Callicoon, the Callicoon Creek and the Delaware River. In-town living doesn't get better than this. Enter on a large wrap-around porch and into a well-built home. You are greeted by an expanse of gleaming wood floors and a large living room and dining room. The updated eat- in kitchen has oak cabinets and granite counter tops. French doors lead into a quiet family room. Upstairs on the 2nd level find 3 bedrooms and a full bath. The 3rd level has 2 bedrooms with an additional bonus room. In the basement you will find the oil furnace, 200-amp electric panel and plenty of room for storage or workshop. This grand home has many original features such as beautiful wood floors, wood trim, 2- story staircase, stained glass windows, and more. Updated features include replacement windows, vinyl siding and a mini-split unit on first floor for heat and AC and fully insulated. Need storage and parking? Outside find a large detached 1-car garage plus a fenced in garden. In-town living is easy, because Callicoon is a fun town with activities including: The Farmers Market, movie theater, a community center offering tennis, swimming pool and pickleball, the Delaware River, great restaurants and shops.

11 Highview Avenue, Callicoon

$899,000
810848 MLS
Callicoon, New York - 5 acre commercial property with 1400 feet of stream front on the Callicoon Creek. Located on NYS RT 17B and next to NYS Rt 97, this is a high traffic/highly visible location. The access for trucks and vehicular traffic is level and provides easy access for loading, unloading and doing business. Currently used as an automotive repair facility, it consists of 4 buildings, large parking area. Main building is 20,000+/- SF consisting of 3 furnaces, 3 phase electric, 5 lifts. 16' high ceilings-many large overhead doors, 2 large garage service areas, body shop with spray booth, lobby entrance, plus many office rooms on 1st & 2nd floor. Building 2 is the tire storage shed (108x45), Building 3 is the vehicle storage garage (45x102), Building 4 is 24x45 and is used for storage. Great level location, 1400 ft on NYS Route 17B and at the intersection of NYS Route 97 - a high traffic location. Let your imagination be your guide, from automotive and industrial to retail sales. This is the gateway to Pennsylvania and the bustling Hamlet of Callicoon on the Delaware River.

4587 State Route 17b, Callicoon

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